YOU ARE MEETING A STRANGER AT THE HOTEL BAR. This is not your regular watering hole: velvet curtains, coffered ceilings, outstretched columns that hold up nothing. Everything is in the style of a ruin that doesn’t know it’s a ruin yet. You finger the thin straw plunged in a gin and tonic, unsure. Are you waiting to be found, or are you supposed to be looking?

On the eighth floor, the room is dark. Shuffling in, you glimpse the outline of a recumbent figure. When the lights come up, a man is lying naked on one of two beds, phone in hand. You wait for him to speak first.

His nakedness is not surprising (men often are when you go up to their rooms); his loneliness isn’t either. The man says he isn’t feeling well. He can’t even play with his penis. He wakes up cold, his nightgown is drafty, the dry air cracks his lips. A middle-aged businessman, there are a hundred other Willy Lomans like him down at the bar. But this man’s skin radiates unexpected softness. His name is Jim.

Jim likes to shit before showering, but can’t always. He likes to watch reruns of funny shows, but each time the credits roll, there’s another maw of emptiness. He has a shadow that follows him, matching his every move, except when it doesn’t. Atop the covers, both Jim’s and the shadow’s legs splay: Their feet overlap in a tender, impermanent alliance.

You can’t imagine anything more excruciating than having your murkier self externalized. It seems like Jim can’t either; when the shadow lopes off to the bathroom, he asks, “Should I really kill him?” The sound of a toilet flushing gives way to a chorus of nervy laughter.

Jim is at once Jim the businessman and Jim Fletcher, the stunning actor who wreaks quiet devastation. His shadow is a catsuited actor named Bob Feldman. This is both a hotel room encounter and a Richard Maxwell play called Showcase. It debuted in 2003, when it seemed like Bush II would be the worst president of your lifetime. Perhaps masculinity felt plush and laughable then, but Maxwell, the playwright and director, has always ambitiously scaled the lives of men.

His most recent work was The Evening, performed at the Kitchen in 2015. It took place on a stage that was also a dive, populated by two barflies, their waitress, and a band. Reviewers seemed displeased with the insinuation that Beatrice, played by Cammisa Buerhaus, was not only a bartender but also a prostitute. Throughout that play she longs to escape; she flatters, cajoles, and soothes the men around her. She freshens their beers and sits on their laps, but mostly, she listens. Until she grabs a gun.

Only a naïve moralist would find sex work more disconcerting than the exhausting labor of listening to men. How many Johns—or Willys or Jims—pay for time just to be heard, to be held?

The Evening muscles its way into your thoughts from the moment Jim sits up, asking the crowd, “How ya’ll doing tonight?” Out of the hush that meets his direct address, you reply: “Good.” Now he is pointing, others are looking. You’re chastised for being “a troublemaker” in the tone that middle-aged businessmen reserve for younger women whose defiance entertains them.

Turning his attention away from you, Jim generously uses your humiliation as an object lesson, to pivot toward the principles of wielding dominance. This, after all, is how you make deals.

Showcase, too, was a kind of power move. It was made for the 2003 Association of Performing Arts Presenters (APAP) conference in New York, an annual networking event-cum-marketplace that takes place in drab hotel conference rooms, where artists brave the indignity of lanyard-strung nametags and vie for their work to be seen by venue representatives rushing between works in progress.

There, perhaps you object thoroughly to the selling and being sold. You also want desperately to be chosen. It is this contradiction that Jim lives three times a night.

After all, the playbook providing white men with the bluster of prerogative and unimpededness is just that, a script. Jim knows his own contrivance—Fletcher knows it too—and both character and actor allow the veneer to fissure, delicately. Jim’s monologue turns to voyeurism, to the enhanced capacities of looking outward by turning off the lights within, and to “Victor”—were they roommates or lovers? He can’t be sure.

Jim goes to the window. His thumbs press into his lower back, making a quiet arc of lightened flesh. He stoops over the desk, rallying himself in the mirror, and begins to dress.

As he puts on his underwear, then his pants—and eventually a shirt, a tie, and a plasticky lanyard—he slowly becomes the man that exists outside the room’s confines, the one who shakes hands and dominates conversations.

The scraping of a belt buckle dragging along the desk is familiar; you know what it sounds like when a man is leaving.

Stories of white-collar workers are often characterized as those of desperation. Such men are the leavers, never the left. But Maxwell’s work is always about desire, the texture of wanting.

If there’s a difference between desperation and desire, it’s hazy, and now the confession comes tumbling out: the cold tile of a bathroom corner, dinner with Victor and his boyfriend escaped, and then Victor’s hands groping where they shouldn’t.

How do you grieve the loss of something you weren’t allowed in the first place? Jim ends cradled in his shadow’s arms, tape-player in hand, singing a tune that does what pop songs do best: want ravenously, unabashedly, on a loop outside time or place.